4-Methylpiperidine-1-carbonyl Chloride → HCID 11594650, compound

HRID 490309Notes

Reaction equation

HRID 490309 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[OH:13])([O-:3])=[O:2].[CH3:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](Cl)=[O:22])[CH2:17][CH2:16]1>N1C=CC=CC=1>[CH3:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:13][C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][N:8]=2)=[O:22])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 178526496HCID 178526496, compound

Product 1

HCID 11594650HCID 11594650, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg (1.12 mmol) of 5-nitro-1H-indazol-3-ol and 180.4 mg (1.67 mmol) of 4-methylpiperidine-1-carbonyl chloride (Example 2) in 20 ml of pyridin were heated under reflux for 5 h and left to stand overnight. Pyridine was distilled off in vacuo, and the residue was dissolved in water and extracted with ethyl acetate. The organic phase was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 48 mg (14%), M+H+: 304.99.

Workup

  1. temperatureunder reflux for 5 h
  2. waitleft
  3. distillationPyridine was distilled off in vacuo
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic phase was concentrated
  7. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-4de51c45bbef4aed849c51e19313a35d
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

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